Cultural intelligence (CQ) has emerged as a promising capability that allows individuals to enhance their intercultural effectiveness. However, little is known about factors and processes supporting its development. In a longitudinal study involving pre- and postintervention measures of CQ, we explored the role of the individual perception of optimal cross-cultural contact and the experience of expectancy disconfirmation. The study was conducted among 212 management students and professionals who partook in an experiential CQ education intervention encompassing cross-cultural contact as part of a university management course. The results of our work reveal that the relationship between participants' perception of optimal cross-cultural contact and CQ development is mediated by the experience of expectancy disconfirmation. When participants perceived optimal cross-cultural contact, which involved a number of conditions including equal status among participants, personalized contact, establishment of common goals, and support of the contact by authorities, they were more likely to experience expectancy disconfirmation. In turn, greater experience of expectancy disconfirmation was associated with greater CQ development. Researchers, educators, and managers who understand the factors and processes supporting CQ development are better equipped to prepare individuals for greater effectiveness in a variety of cultural contexts.